Ha, it's this year now, so DH can't tell me I'm thinking too far ahead. Sure, trying to figure out a summer vacation for NEXT year is too far away, but for THIS year it's perfectly fine, right??!!
Instead of flying back to the US for 3 weeks I want to do our 'big' vacation in Italy this year. We go to ITaly once or twice a year, but it's always just a long weekend (3-4 days) which makes us stay in Milan, because there's so much family to see and venturing out of the city takes too much of our precious time.
What I figured now is to still take Milan as our home base, but venture away for day or multi-day trips.
My idea now is:
- take a 3 - 4 day trip by train from Milan to Cinque Terre. Sleep in a different village each day
- rent a car and take a 3-4 day trip into Tuscany. I want to visit Sarripoli (near Pistoia) as DH's family (grandma's side) is originally from there and he used to spend time there as a little boy) and Colle di Val d'Elsa near Siena as a friend of mine lives there. We've both been to Florence and Pisa, so we can really stick to the cute little tuscan towns.
- take a 2 day/1 night trip to Venice by train (only 1.5-2 hr train ride, leave morning day one, come back evening day 2)
In between all these trips have 2-3 days in Milan each time, possibly being able to venture out of the city a little for an afternoon or so, but mostly just hang out with family, eat, do laundry, eat, go to awesome food markets or antique markets, eat, go out for drinks eat, well that sorta stuff.
We can both take 3 weeks of vacation in a row, so I think we have plenty of time to do this and not be rushed.
What do you think, sound fun?
(P.S. we both hate the extremely rushed 'we're in Paris so it must be tuesday' kind of traveling and aren't into doing super touristy stuff all the time. So if you have suggestions, please bear that in mind!)
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What I'm looking forward to in 2012:

Eating our way through (northern) Italy on vacation
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Re: Figuring out our big vacation this year (Italy experts come in!)
When I went to Cinque Terre with my fam, we stayed in the less touristy town of La Spezia. I can't remember much about it, but we were pretty satisfied. From there you can take a boat or train to the Cinque Terre villages.
Near Siena there is a little town called Monte Riggione; less touristy than San Gimignano (which is also very nice).
That's all I got for now. I'll try and think of more soon!
I spent 3 weeks in Italy 4 years ago (pre-DD) and it was lovely. I just mosied along at my own pace. I did a yoga retreat in Tuscany for a week, explored around the area during and after the retreat (including Siena and San Gimigniano- both are beautiful), went down to Naples to hang out with a friend who was working there, did a lot of day trips from Naples (Capri, Pompeii, etc.) and then circled back up to Rome for several days before leaving. Some of my favorite days were ones spent in Naples just shopping for fresh veggies and talking to shop keepers about the best way to make meatballs or tomato sauce.
In Tuscany, I recommend I Selvatecci winery for a tour (if you're into that) and staying at Il Burchio for a night or two. It's a short drive from I Selvatecci and you can go horse back riding at Il Burchio. The pace is very laid-back.
Cecilia arrived 12 October 2012
Sushi: My friend who lives near Siena actually just started a business doing Tuscan food tours. She was born and raised there and has been giving those kinds of tours for a while , but as she recently got laid off from her 'day job' she decided to make her job out of it.
If you're interested in doing something like that for a day or so, let me know, so I can get you 2 in touch.
The others: thanks for the tips! IT's great to read things people enjoyed. I'd love to go horse riding, however the chances of me getting DH on a horse are slim. A wine tour on the other hand, will definitely make him happy!
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What I'm looking forward to in 2012:
Eating our way through (northern) Italy on vacation
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Yum. That sounds really interesting. We're just starting to think about things, so I'm open to suggestions at the moment. I'd love to know more about!
Cecilia arrived 12 October 2012
Sounds like you'll have some time in Milan; Verona's not a bad day trip from M and is my favorite city in IT (almost 3yrs into it).
In Tuscany, I like Radda and Montepulciano best. If you're training it, monte p is farther but more accessible than radda.
I spend a good deal of free time (read one weekend/mo in either Tuscany or Umbria) so I'm best w hotels there. We live outside of Naples and I often work in Rome, so I've got a decent knowledge of sights & restaurants. Let me know, of I can help!